Chester Hotel Guide - 4 Stars Hotels in Chester, Vermont

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chester 4 Star Hotels

Next weekend
12 Jun - 14 Jun
In two weeks
19 Jun - 21 Jun

Our top choices for Chester 4-star hotels

Lobby

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (582 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."
United States
Christopher
The price is Rp7.737.444
Rp9.304.773 total
includes taxes & fees
9 Jun - 10 Jun
Woodstock Inn & Resort
Meeting facility

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG
4.0 star property
Manchester Village Historic District
9.4 out of 10, Exceptional, (848 reviews)
"Great spot in Manchester! Perfect for families or couples!"
United States
kathleen
The price is Rp2.993.976
Rp4.047.278 total
includes taxes & fees
14 Jun - 15 Jun
Kimpton Taconic Hotel by IHG
House (Meadow) | View from room

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa
4.5 star property
Manchester Village Historic District
7.4 out of 10, Good, (634 reviews)
"The hotel was beautiful!"
United States
Lorajean
The price is Rp2.535.362
Rp3.802.435 total
includes taxes & fees
22 Jun - 23 Jun
The Equinox Golf Resort & Spa
Hallway

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,001 reviews)
"Great stay here "
United States
Sophia
The price is Rp5.989.756
Rp7.250.111 total
includes taxes & fees
13 Jun - 14 Jun
On The River Inn
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (284 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
The price is Rp3.652.290
Rp4.017.699 total
includes taxes & fees
8 Jun - 9 Jun
The Jackson
Restaurant

The Reluctant Panther Inn and Restaurant

The Reluctant Panther Inn and Restaurant
4.0 star property
Manchester Village Historic District
9.8 out of 10, Exceptional, (366 reviews)
"Spacious room with sitting area and fireplace."
United States
Jean
The price is Rp4.130.244
Rp4.543.268 total
includes taxes & fees
9 Jun - 10 Jun
The Reluctant Panther Inn and Restaurant
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (40 reviews)
"The hot tub was so amazing"
United States
Mark
The price is Rp2.353.698
Rp2.565.531 total
includes taxes & fees
8 Jun - 9 Jun
Four Columns Inn
Interior

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (79 reviews)
"Great location, service and restaurant "
United States
LUDJANE
The price is Rp3.374.716
Rp4.342.167 total
includes taxes & fees
21 Jun - 22 Jun
The Inn at Weathersfield
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (58 reviews)
"Fabulous home, breakfast, staff, and location. Excellent value! Will definitely be back!"
United States
Mary
The price is Rp5.123.126
Rp5.635.348 total
includes taxes & fees
9 Jun - 10 Jun
Inn on Putney Road
Restaurant

The Hermitage Inn Vermont

The Hermitage Inn Vermont
4.0 star property
West Dover
8.8 out of 10, Excellent, (18 reviews)
"Wonderful stay! Loved the amenities!"
United States
Keely
The price is Rp5.803.083
Rp6.383.392 total
includes taxes & fees
14 Jun - 15 Jun
The Hermitage Inn Vermont
Exterior

Seesaw's Lodge

Seesaw's Lodge
4.0 star property
Peru
10.0 out of 10, Exceptional, (26 reviews)
"Great cabin with an even greater staff!!"
United States
Eyasser
The price is Rp3.467.241
Rp3.779.292 total
includes taxes & fees
8 Jun - 9 Jun
Seesaw's Lodge
Exterior

Solitude Village at Okemo by Vail Resorts

Solitude Village at Okemo by Vail Resorts
4.0 star property
Clock Tower Base Area
7.8 out of 10, Good, (35 reviews)
"Great location!"
United States
DIEN
Solitude Village at Okemo by Vail Resorts
Property grounds

Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property
4.0 star property
Clock Tower Base Area
8.8 out of 10, Excellent, (26 reviews)
"I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place "
United States
Kathia
Winterplace at Okemo, A Vail Resorts Property
Room, 1 Queen Bed, Garden View | Mountain view

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (41 reviews)
"The room was wonderful. SO spacious and well-appointed, extremely clean. Loved the excellent bedding, the soaking tub, the perfect water pressure in the shower. We did not expect the flat-screen TV, so it was a treat to have. Don't let the lack of restaurant bother you: There are plenty of great choices around, though you have a bit of a drive. For a leisurely romantic weekend, I can't think of a better place. "
United States
Debbie
The price is Rp3.351.991
Rp3.653.733 total
includes taxes & fees
22 Jun - 23 Jun
Windham Hill Inn
Terrace/patio

The Village Inn of Woodstock

The Village Inn of Woodstock
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (97 reviews)
"Breakfast was good. They give you a choice out of 2 of 3 things. It’s nice to have a variety, especially when staying somewhere for several days. I believe we rented the largest room, that had an attached sitting/ tv room and balcony. Well, everything was great except the bathroom was really small. Prob why it’s not in any pictures."
United States
Julie
The Village Inn of Woodstock
Front of property – evening/night

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (105 reviews)
"Great stay"
United States
Wayne
The price is Rp5.431.361
Rp5.893.083 total
includes taxes & fees
8 Jun - 9 Jun
Chesterfield Inn
Exterior

The Woodstocker B&B

The Woodstocker B&B
4.0 star property
Woodstock
10.0 out of 10, Exceptional, (51 reviews)
"This food at this property is amazing!! I would come back any day, the bread and entire menu is incredible. The zagat should try their breakfast! "
United States
Kavina
The Woodstocker B&B
Apartment (3 Bedrooms) | Interior

Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!

Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
4.0 star property
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful four night stay at this great condo! Perfect if you are skiing out of Okemo! The condo was beautiful, clean and the host Bill was so communicative and responded to texts immediately. The gym and spa was also an added bonus! Great time! "
United States
Nipa
Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
Apartment (2 Bedrooms) | Interior

Bromley Mountain Escape w/ 2 Balconies: Hike & Ski

Bromley Mountain Escape w/ 2 Balconies: Hike & Ski
4.0 star property
Bromley Mountain
6.0 out of 10, (1 review)
"The property is low cost in a nice area of Peru seconds from Bromley Mtn. BUT the property needs some serious updating -No AC. The host was more than accomodating. "
United States
Chris
Bromley Mountain Escape w/ 2 Balconies: Hike & Ski
Apartment (2 Bedrooms) | Interior

Dover Condo w/ Grill & Balcony: 3 Mi to Mt Snow!

Dover Condo w/ Grill & Balcony: 3 Mi to Mt Snow!
4.0 star property
West Dover
Dover Condo w/ Grill & Balcony: 3 Mi to Mt Snow!
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Chester.
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

3567 Main Street Manchester VT
Get rates
7.4/10 Good! (3 reviews)
Still don't see what you're looking for?
See all properties in Chester.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Chester

Nestled in a relaxing small-town setting, Chester invites visitors to explore DaVallia Art & Accents and browse handcrafted treasures at Bonnie's Bundles Dolls. Outdoor enthusiasts can enjoy nearby Stoughton Pond Recreation Area or take a scenic drive to Lowell Lake State Park and the charming Vermont Country Store.

See all hotels in Chester
Chester Suspension Bridge

Top Chester Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"Great stay. Beautiful location"
Brian 2-night trip
Posted 1 day ago
On The River Inn
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4/10 Poor
"dirty room and overcapacity. No breakfast"
Laura 2-night trip
Posted 5 days ago
Kimpton Taconic Hotel by IHG

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Chester?
With Expedia's sort and search filters, scoring a terrific deal on a 4-star hotel in Chester just got simpler. Start by keying in your chosen arrival date and length of your holiday. Then list the results by price and choose a property that best fits your style and budget.

  • Search for the lowest price from Rp7.765.399

What's the difference between 5-star and 4-star hotels in Chester?
Offering an inviting traveller experience and upscale décor, 4-star hotels are an excellent option for your Chester break. These kinds of accommodation generally come with loads of handy amenities that make it a breeze to unpack and unwind — think complimentary bathrobes, gyms and pools. Or live the high life at a 5-star hotel designed to indulge you in luxury perks and amenities. On-site health clubs, oversized bathrooms and gourmet dining are typically featured at these deluxe retreats.
Does Chester have any 4-star all-inclusive resorts?
Finding holiday bliss in Chester is as easy as entering in your dates and selecting our "All inclusive" filter. Stay and play where almost everything is already taken care of like your meals, accommodation, entertainment and activities, or opt for a standard 4-star resort in or around this top destination.